Reap the benefits of what you have gained so far, most likely almost tax free.

I like to know everything I need to know and gain tips and advise on how to find a starter homer hat meets most of my needs. 

This is commonly referred to as the BRRRR strategy.If you are looking to grow a portfolio to gain passive income to replace your current income this is a perfect strategy to use.  

I am not necessarily saying you have to use all of your gains from the primary residence for a new property. 

I will list the numbers:current rent $1950/month (going to $2000 in about 6 months at end of 2 yr lease)My expenses: annual taxes $7950 ($662/month)                        Heloc balance $170k interest currently 5%                        land lord policy $1150/ year                        Self managed                        Maintenance : has averaged $300-400 per year.Reasons I am considering sale :   1) property is currently worth about $270k (making me feel roi is low).                                                           2) property has a pool which is a liability that I'm not completely comfortable with.                                                           3) property has a heloc balance against it of about $170k that I technically cannot deduct the interest                                                                       because it wasn't used for the property or any other rental.                                                           4) Tax treatment: my understanding is if you sell it having lived in it 2 out of last 5 years the capital gains                                                                 would be exempt. 

So for the extra $20 a month I would have to invest into wifi extenders but end of the day I will be gaining..

I am trying to see different ways of marketing the property to gain investors interest.

If it's owner occupied, there is the $250K single, $500K husband and wife capital gain exemption. 

No, just like we can't capitalize and depreciate increases in value in a rehab beyond what was actually incurred.Both are unrealized gains on the underlying asset which have no current tax effect. 

Good Morning Angela, I am a Realtor in Florida and I understand this completely. ( I am not one of those agents) Thank goodness, I would suggest not letting them know what you intend on doing as they only see $$$ signs, and if you are looking for something off-market then their commission will be less,  I suggest looking for the deals yourself through Zillow, Make me move is a for sale by owner, your county records, for pre-foreclosures,  do your research first, then contact an agent to gain access to a property you may want.